DE2237633C3 - Verfahren zur Herstellung von Copolymeren auf der Basis von Alkylvinyläthern und ihre Verwendung - Google Patents
Verfahren zur Herstellung von Copolymeren auf der Basis von Alkylvinyläthern und ihre VerwendungInfo
- Publication number
- DE2237633C3 DE2237633C3 DE2237633A DE2237633A DE2237633C3 DE 2237633 C3 DE2237633 C3 DE 2237633C3 DE 2237633 A DE2237633 A DE 2237633A DE 2237633 A DE2237633 A DE 2237633A DE 2237633 C3 DE2237633 C3 DE 2237633C3
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- copolymers
- alkyl vinyl
- cyclopentadiene
- isopropylidene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920001577 copolymer Polymers 0.000 title claims description 16
- -1 alkyl vinyl ethers Chemical class 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 11
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 claims description 6
- 238000004073 vulcanization Methods 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229920001971 elastomer Polymers 0.000 claims description 3
- 239000000806 elastomer Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- MVKNKYUEMVWBOK-UHFFFAOYSA-N 3-propan-2-ylidene-1,2,7,7a-tetrahydroindene Chemical compound C1C=CC=C2C(=C(C)C)CCC21 MVKNKYUEMVWBOK-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 150000004291 polyenes Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 229920000642 polymer Polymers 0.000 description 14
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000004448 titration Methods 0.000 description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001993 dienes Chemical class 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004455 differential thermal analysis Methods 0.000 description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- SMBYEXNJVNACSW-UHFFFAOYSA-N 2,3,3a,7a-tetrahydro-1h-indene Chemical compound C1=CC=CC2CCCC21 SMBYEXNJVNACSW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 241000863032 Trieres Species 0.000 description 1
- WRYNUJYAXVDTCB-UHFFFAOYSA-M acetyloxymercury Chemical compound CC(=O)O[Hg] WRYNUJYAXVDTCB-UHFFFAOYSA-M 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005496 tempering Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- BHAROVLESINHSM-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1.CC1=CC=CC=C1 BHAROVLESINHSM-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2701571 | 1971-07-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2237633A1 DE2237633A1 (de) | 1973-02-15 |
| DE2237633B2 DE2237633B2 (de) | 1977-12-01 |
| DE2237633C3 true DE2237633C3 (de) | 1978-08-17 |
Family
ID=11220771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2237633A Expired DE2237633C3 (de) | 1971-07-31 | 1972-07-31 | Verfahren zur Herstellung von Copolymeren auf der Basis von Alkylvinyläthern und ihre Verwendung |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3853829A (OSRAM) |
| JP (1) | JPS5338313B2 (OSRAM) |
| AT (1) | AT332644B (OSRAM) |
| AU (1) | AU474224B2 (OSRAM) |
| BE (1) | BE786620A (OSRAM) |
| CA (1) | CA989541A (OSRAM) |
| CH (1) | CH551459A (OSRAM) |
| CS (1) | CS178874B2 (OSRAM) |
| DD (1) | DD99171A5 (OSRAM) |
| DE (1) | DE2237633C3 (OSRAM) |
| ES (1) | ES405821A1 (OSRAM) |
| FR (1) | FR2149110A5 (OSRAM) |
| GB (1) | GB1348213A (OSRAM) |
| HU (1) | HU165838B (OSRAM) |
| LU (1) | LU65792A1 (OSRAM) |
| NL (1) | NL152875B (OSRAM) |
| PL (1) | PL71075B1 (OSRAM) |
| RO (1) | RO63337A (OSRAM) |
| SE (1) | SE381470B (OSRAM) |
| TR (1) | TR16988A (OSRAM) |
| ZA (1) | ZA725070B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5146212A (ja) * | 1974-10-17 | 1976-04-20 | Fuji Kagaku Shikogyo | Chookingupeepaa |
| CA3046464A1 (en) * | 2016-12-16 | 2018-06-21 | Novoset, Llc | Resin compositions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3179717A (en) * | 1960-06-01 | 1965-04-20 | Edward J Dufek | Coating compositions comprising polymers of vinyl ethers of polyunsaturated fatty alcohols |
-
0
- BE BE786620D patent/BE786620A/xx unknown
-
1972
- 1972-07-11 AU AU44430/72A patent/AU474224B2/en not_active Expired
- 1972-07-14 RO RO7200071616A patent/RO63337A/ro unknown
- 1972-07-19 GB GB3385472A patent/GB1348213A/en not_active Expired
- 1972-07-24 ZA ZA725070A patent/ZA725070B/xx unknown
- 1972-07-24 CA CA147,811A patent/CA989541A/en not_active Expired
- 1972-07-24 CH CH1103572A patent/CH551459A/fr not_active IP Right Cessation
- 1972-07-25 TR TR16988A patent/TR16988A/xx unknown
- 1972-07-26 FR FR7226807A patent/FR2149110A5/fr not_active Expired
- 1972-07-26 LU LU65792D patent/LU65792A1/xx unknown
- 1972-07-28 DD DD164741A patent/DD99171A5/xx unknown
- 1972-07-28 HU HUSA2383A patent/HU165838B/hu unknown
- 1972-07-28 US US00275935A patent/US3853829A/en not_active Expired - Lifetime
- 1972-07-29 PL PL1972157011A patent/PL71075B1/pl unknown
- 1972-07-31 AT AT661572A patent/AT332644B/de not_active IP Right Cessation
- 1972-07-31 NL NL727210510A patent/NL152875B/xx unknown
- 1972-07-31 CS CS7200005353A patent/CS178874B2/cs unknown
- 1972-07-31 DE DE2237633A patent/DE2237633C3/de not_active Expired
- 1972-07-31 ES ES405821A patent/ES405821A1/es not_active Expired
- 1972-07-31 JP JP7605372A patent/JPS5338313B2/ja not_active Expired
- 1972-07-31 SE SE7209974A patent/SE381470B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE786620A (fr) | 1973-01-24 |
| AU474224B2 (en) | 1976-07-15 |
| AT332644B (de) | 1976-10-11 |
| NL152875B (nl) | 1977-04-15 |
| CS178874B2 (en) | 1977-10-31 |
| JPS5338313B2 (OSRAM) | 1978-10-14 |
| SE381470B (sv) | 1975-12-08 |
| ZA725070B (en) | 1973-04-25 |
| JPS4825088A (OSRAM) | 1973-04-02 |
| TR16988A (tr) | 1974-03-06 |
| CH551459A (fr) | 1974-07-15 |
| NL7210510A (OSRAM) | 1973-02-02 |
| HU165838B (OSRAM) | 1974-11-28 |
| DE2237633B2 (de) | 1977-12-01 |
| ES405821A1 (es) | 1975-07-16 |
| FR2149110A5 (OSRAM) | 1973-03-23 |
| DE2237633A1 (de) | 1973-02-15 |
| LU65792A1 (OSRAM) | 1972-11-28 |
| ATA661572A (de) | 1976-01-15 |
| CA989541A (en) | 1976-05-18 |
| RO63337A (fr) | 1978-09-15 |
| PL71075B1 (OSRAM) | 1974-04-30 |
| AU4443072A (en) | 1974-01-17 |
| US3853829A (en) | 1974-12-10 |
| DD99171A5 (OSRAM) | 1973-07-20 |
| GB1348213A (en) | 1974-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |